© 2017 by Intrepid Media Inc.
All rights reserved.
Welcome to The Jump. Thanks for taking the time to read this book.
THIS IS A PREVIEW of another book called Entrepreneur Life. My hope is that you’ll read this first, get something out of it, and then put up the money for the whole book. You can get that book where you got this one, or anywhere you can buy books.
So, I know that if you’re reading this intro, there’s something in you that finds startup appealing. Maybe you already know a little or a lot about startup, but you’re turned off by the way startup people talk about startup.
I totally get that. I feel that way too.
Here’s the antidote.
The Jump, and in longer form, Entrepreneur Life, is about a new way to look at entrepreneurism, and it’s about independence, freedom, growth, achievement, happiness, and success, no matter what it is that you start.
The earlier chapters link to the earlier part of startup. That’s what you’re getting here with The Jump. As you get deeper into running your own company, the later chapters of Entrepreneur Life will apply a little more directly. But I hope it’s all valuable and applicable, no matter where you are on your journey.
Look, there are a lot of people out there like you. Startup is not an exclusive club. It’s not a rite of passage. It’s not about board seats and billions of dollars. It’s about waking up every day and doing what you love.
That’s what this book is about.
Who Am I?
ve been an entrepreneur for over 20 years, almost my entire career. That first year though, right out of college, that was spent at a corporate consulting company where I wore a suit every day, worked from 9:00 to 5:00, had three different bosses, and hated every minute of my life. I quit that job and took the next job I found that I thought might be fun. That job was at a startup.
I lucked into startup. People shouldn’t have to luck into startup.
Over the last 20-plus years since, I’ve done 10 startups, some on my own, some with others. Some were great successes, some were massive failures. Most were somewhere in between.
Currently, I’m at Automated Insights, a company that makes software that automatically writes narrative content from raw data. I’ve been at Ai since 2010, and while I was there I founded ExitEvent in my spare time. ExitEvent is a startup network and news source, and in three years it became the most widely-read startup media site in the Southeast. I sold ExitEvent in 2013. Ai was acquired in 2015.
Since then, I’ve been investing in startups, meeting with founders, mentoring, advising, all of that cool stuff you get to do when you exit. But none of that made sense to me. I was able to help a handful of people at a time, and I found I was saying a lot of the same stuff over and over.
I needed to scale. This book is a part of that effort.
Another part of that effort is Teaching Startup (teachingstartup.com). I’m not going to pimp Teaching Startup here, but visit it and join it. If you like this, you’ll like that.
I also continually crank out more content like this at my website at joeprocopio.com. Visit that too.
But enough about me…
When I first started this book-writing journey, I didn’t have a lot of focus. I pretty much just had a mission:
I want to take everything I’ve learned over the last 20 years of doing hard things, and present those life lessons, up to date and easily and enjoyably understood, to help you do whatever it is you truly want to do, whether you know exactly what that is or not, probably more so if you don’t.
That’s a lot to put into a book title.
I’ve done this kind of writing-as-help thing before. In fact, I created an entire company out of making it easier and more fulfilling to be an entrepreneur. That was ExitEvent, which I founded in 2010 and sold in 2013, spending no more than five hours a week on it at any given time.
I don’t want to re-do ExitEvent. I’ve done it. It was fun. A big media company is doing it now, and they’re doing it better.
I’m still an entrepreneur. I still want to help entrepreneurs, but not just entrepreneurs.
I’m doing that with Teaching Startup, bringing that 20-plus years of entrepreneurism to everyone, regardless of whether you’re an entrepreneur or not. In fact, Teaching Startup works just as well if you’ve never tried startup or if you’re a serial entrepreneur with a couple of successes already under your belt.
I do other hard stuff too -- mentoring early-stage entrepreneurs, investing, parenting twins (plus one more), developing a writing career, staying fit, even playing in a band.
Am I an expert in any of these? I doubt it. Plus, if you came to me and asked for specific advice to deal with your kid, I’d probably duck you.
What I am an expert in, so to speak, is satisfaction. I’m really good at being happy. Not happy like I’m all rainbows and unicorn farts all the time, but happy with what I’m doing, where my life is going, what the future holds for me. That kind of happy.
That all relates to startup.
However, the only topic I find more ripe for phony guru-ism than startup is the more generic and touchy-feely self-help genre.
Dude. So not me.
So, much like I had to turn startup advice on its head with ExitEvent, I’m trying to do the same thing with Teaching Startup. And with this book.
Teaching Startup focuses on the nuts and bolts -- how to get your company from point A to point B.
This book will talk about how to get YOU from point A to point B.
See, for the longest time, I kind of thought my happiness and satisfaction was just a fluke. Maybe I’m just an eternal optimist, maybe I’m just freaking lucky, maybe I’m just too dumb to know any better.
Maybe I’m just wired differently.
All of that is true, to an extent, but it isn’t the whole story, because none of it is by accident. It all has to do with running my own show.
It’s not being an entrepreneur that gives me satisfaction. The work is harder, it doesn’t provide as much freedom as you’d think, and it comes with way less perks.
But for the most part, I’m calling my own shots. I’m in control. I don’t want a corner office and a fancy title because I’ve learned that’s phony, just as phony as that theory about how if you want something hard enough, it’ll happen.
To get all conspiratorial with it: All that definition of success stuff was invented to keep you asleep.
I’m not happy because I’m rich. Or young. Or good looking. I’m zero for three on those. I’m happy because I have everything I want. And I have everything I want mostly because I’ve learned that I don’t want most things people want. I want what I want.
I’m independent. I’m entrepreneurial.
What’s more is, you probably are too.
It doesn’t matter if you want to be an entrepreneur or a writer or a corporate leader or a homemaker or a priest or a beach bum. What I’m writing will serve you well, because it speaks to those traits that everybody has and those things that everybody wants.
Welcome to the army of entrepreneurs.
Despite what conventional wisdom would have you believe, there are a lot of us. In fact, there are more of us than them.
And we’re growing.
We’re just not all awake yet.
There are four key components to an entrepreneurial life -- Growth, Achievement, Success, and Happiness. If you think about how we traditionally pursue goals, these components seem to flow in order -- the more you grow, the more you achieve, the more successful you become, the happier you will be.
But that isn’t always the case. Nor should it be.
Growth is mandatory, and I honestly didn’t realize how important this concept was until I had kids. Kids start from zero. You don’t get a sense of what growth truly means until you have to tell a kid how to put on his socks.
But life is about growth. There are growth points with every difficult undertaking, there is opportunity with each mistake, and there are lessons in every failure. I’m constantly telling my kids to take their shot, to make their mistakes, to fail quickly and often. Not coincidentally, this is the same advice I give to anyone who believes they have an entrepreneurial mindset.
Achievement gives growth meaning. If growth is magnitude, achievement is direction, and it can be anything you want to tick off a list. Training for distance running brings growth, but achievement is your first 10-mile run. Starting a company brings growth, but achievement is selling your first product or crossing a revenue number or hiring your first employee.
Success seems pretty obvious at first glance, but the thing about success is it can mean different things to different people at different times in their lives. Success may be financial, or familial, or freedom.
Happiness is the one thing that everyone can agree on, definition-wise, but it’s also the hardest to create. You know when you’re happy, and you should have a pretty good idea of what makes you happy.
The problem is… most people think the wrong things are going to make them happy.
There’s another reason I chose these four concepts. The super tricky thing about them is that they also flow in reverse. The happier you are, the more successful you become, the more you achieve, the more you grow.
I haven’t discovered fire here. In fact, pursuing happiness to get to success instead of the other way around is an oft-spewed inspirational quote.
But like most inspirational quotes, you’re just expected to nod your head and figure it out. You never get the why and how. So let’s take a look at that.
The novice takes the former path, starting with growth and ending with happiness. There's no getting around that because, like a kid, at the beginning we don't know anything about anything. The accomplished independent, the successful entrepreneur, the established artist, the experienced builder -- these people work backwards most of the time.
Happiness doesn’t come from money. Let me put it this way: Most people think that if they have enough money, they’ll wake up happy every morning. The crazy truth, and it even seems unfair in this day and age, is that if you wake up happy every morning, the money will come.
This does not happen by magic. When you’re happy, you start doing the right things for the right reasons. All of your time and energy becomes focused on one mission.
Moments make me happy. Time makes me happy. Pride in my kids and my work makes me happy. My wife makes me happy. Doing new, fun, exciting stuff makes me happy. Some television shows make me happy. Most of this is free.
Success is the ability to remain happy. That comes from the inside. You can’t buy it, but you sure as hell can work for it. These days, my own definition of success is the amount of time I have to do whatever I want.
One of my greatest fears had always been that I was going to wake up one day 15 years later and realize I had been pursuing the wrong dream. Now what I pursue changes often, sometimes weekly, because I’ve stopped defining success with money and title and status and recognition and started following my happiness like Jack Sparrow with his compass.
Achievement becomes something you can’t quantify, but something you can pretty easily identify. These will be your own unique achievements, and no one else’s. You can’t lose out on that big award or promotion because no one else is gunning for your achievements.
It’s kind of an odd way to put it, but my achievements are on Facebook, not LinkedIn. I can scroll through my own profile and list a dozen or so big achievements every year. There are other achievements that are more subjective, like that time I tried that thing and failed and shrugged it off, or that time a mountain of crap fell on me and I got through it with my sense of humor intact, or those times I woke up excited to face the day for no good reason.
Growth comes when you string enough of these achievements together. As you pile up more of these uniquely personal accomplishments, you’ll become a bigger, better, and more well-rounded person. These are the big lessons you learn only after learning a million of the small lessons.
The beautiful outcome when working backwards like this is that every time you grow, you become happier, and the cycle starts all over again. It becomes self-perpetuating, and in that sense, it’s almost self-fulfilling.
The truth is it works both ways. Your growth can lead to happiness and your happiness can lead to growth. It takes a while before the reverse can work for you, but you’ll know how to do it when you get there.
I don’t believe in self-help, and I don’t believe in top 10 lists. But I’m constantly confronted with what amounts to terrible self-help advice shoved into a top 10 listicle.
At some point, you have to stop hating the game and start hating the player, so here are 10 things you can do, today, to start working towards success at the things you want to do with your life.
This won’t change your world, it won’t make you richer, better-looking, or smarter, and there are about 1000 more where these came from. But these are 10 changes you can make today. Now. When you get to the end of this chapter, do these things. You’ll be happier.
Oh, if you already do any of these things, just do them harder.
1. Release yourself from worry -- whether that be financial worry or career-path worry or whatever. The only goal you should have in life should be your happiness, which is going to come from HOW you lead your life, not what you do with your life.
2. Get yourself a mission. You need an essential set of strategies that are unique to you. This is critical. None of the strategies should be “network more” or “lose weight” or “be thankful for what I have.” They should all have action attached. Put some thought into this.
3. Stop listening to what other people tell you defines success. No one has the roadmap to your success except you. There are common strategies and paths to get you to operate at peak efficiency. Listen to those. No one has all the answers. Except you.
4. Stop focusing on your limitations. You can’t be all things to all people, but you can be all things to yourself. And you can be most things to the people you care about. A lot of this can be accomplished just by showing up. The rest of it will present itself when the time is right.
5. Give yourself time. If you don’t have enough time to do the things you want to do, figure out how to make that time. I guarantee you that there are at least a dozen things you do on a daily basis that you don’t have to do. We all tend to get OCD about our routine. Don’t do this. Stop wasting time on those things that seem like they’re moving you forward but are just comfortable tasks you can tick off a list when you’re done.
6. Consider the fun quotient of every new thing you take on. There’s this puritan work ethic that still exists in modern day life that drives us to feel guilty and/or silly if we’re not beating ourselves up every day. This is ridiculous. If you truly believe in what you’re trying to accomplish, your life gets more fun. I’ve turned down opportunities strictly on the basis that they’d be no fun. And some of those wound up being successes. I have no regrets and I’m happy for everyone involved. It just wasn’t my thing.
7. Surround yourself with independent thinkers and doers. You can’t live your own life if you’re constantly being told what you must look like, sound like, act like, and how to think. This covers everything from television shows and commercials to the music you listen to and the books and articles you read to the social networks you sign into every day.
8. Stop worrying about how you come across. What's important about you is what you can contribute -- it's what you say, not how you say it. If someone doesn't get you, fine, someone else will. Find your audience and play to it.
9. Don’t strive to be different, strive to be you. You are unique, and therein lies your value. Example: I don't dress to the occasion anymore, I dress for comfort, in order to be at my best -- and that can mean different things. If I'm speaking, I hate being in a suit. It sucks. I feel like a 12-year-old at an adult party. If a T-shirt makes me feel more like me, I put on the T-shirt, and I kill. If everyone else is in a suit, so be it. The reverse is also true, and that's key.
10. Don’t shoot yourself in the foot. A lot of independent-minded people will struggle very hard to make sure they don’t succeed. They will make sure that they thumb their nose at opportunity at every chance. There’s something awful to this, like your marketing approach tries so hard to look like anti-marketing that it’s its own form of marketing. Do what’s right, not what people will think is cool.
There are people in this world who spend their entire lives, or at least a great chunk of their lives, working towards one awesome, high-reward goal. I’m talking about the traditional single-focus pursuits, like athletes, doctors, or priests.
I use those three examples to make it clear I’m not railing against some ends-justify-the-means career choice for the sake of money, fame, and power.
My point is that it doesn't matter if we're talking about an NFL Quarterback -- all the adulation and guaranteed-money contracts. Or a doctor -- decades of education and sacrifice to live a stressful vocation but one that is still respected and provides well. Or a priest -- when done right, it means giving up ALL the worldly garbage.
I’m not talking about what those people WANT. I’m talking about WHO THEY ARE.
I respect the hell out of these types people. The dedication, the sacrifice, the dogged pursuit of a single outcome, all or nothing. But that’s not me.
It used to be. I used to have goals. Now I don’t.
Why am I leaving my success to chance?
I started to realize that the brick wall I kept running into in pursuit of my goals was more than everyday entrepreneur’s cramp. I started staring the void right in the voidhole, and I didn’t like what I saw. So I started attacking it.
I hit it logistically. One year I took my list of goals and I broke down each goal to get to its core, the root, the reason I wanted the thing in the first place. I stared at my list, I rearranged it, I broke out the subtasks and wrote new ones. I hit it creatively, changing location, perspective, language, tone. I erased the whole thing and started over.
Each time I wound up with a slightly differently worded version of the original list.
Then it hit me.
Goals aren’t for entrepreneurs. Sitting down and writing out a list of goals is actually the exact opposite of entrepreneurism.
And the thing is, I already knew that.
Think about the doctor. Four years of pre-med with a sub-goal of finishing at or near the top of the class. All of that breaks down into a single metric (grades) and single-mindedness of studying and hard work. There are no detours, little experimentation, and not a lot of creativity on this journey. Then there’s getting into the right medical school, landing the right residency, and so on. It’s the same for everyone, at every point in the timeline. No deviation.
If you fail at any of these points, you either rewrite a watered-down version of your original goal or abandon it outright. I can’t handle that. That scares the crap out of me.
When you’re an entrepreneur, every day becomes a series of never-ending choices . It's also a series of never-ending tasks toward continually shifting goals. Sometimes it's external -- like I'm sure Steve Jobs didn't realize he had the iPhone anywhere in the back of his mind in the early 1980s. But it was there, somewhere, in the way he pushed and molded and evolved the company from those early days.
When I talk about what I want to do as an entrepreneur, I can’t even get it into an unembarrassing sentence. I want to be awesome, fire the rocket, burn down the system, and rebuild it so that it works for more people.
It’s like a surfer-hippie-NASA guy. Not a doctor.
This is not an easy thing for people to grasp, even entrepreneurs. But it is something that will remind you of itself when you do it the wrong way for a couple months.
So don’t do that. Stop worrying about your goals. They’re there. They just haven’t taken shape yet.
Fear is real. Fear is easy to talk about when you’re not experiencing it, but it can be crippling when you’re facing it. We all have to deal with it, and if you want to succeed at anything worth doing, you can’t ignore it. You can’t beat it. But you can use it.
I like to think of myself as afraid of a very small number of things. The big one is flight. I’ve been afraid of flying for about 15 years, although I’ve flown about 200 times, and the first 100 or so were without the slightest pang of terror.
There was never any direct trigger that brought about my fear. It just started one day and got progressively worse. It took forever for me to realize, only in this past year, that my fear of flying is actually claustrophobia, exacerbated by turbulence.
Again, no great discovery or methodology. I figured it out myself one day, on a hunch.
It doesn’t make the mid-air tremors any easier to ignore. I still freak out on the inside during really bumpy flights. But now that I know exactly what it is I’m afraid of, I can get on a plane without dreading it for days or even weeks before the flight.
The dread was the killer part. From the moment I knew I had to fly until the moment I landed, I was racked with small to massive amounts of dread. Now, flying just sucks for about 50% of however long the flight is. I can so totally live with that, and even enjoy smooth flights. I take the aisle seat and I get up a lot. It bugs the attendants but it does the trick.
So claustrophobia, cockroaches, hospitals, and moldy food. End of list.
Fear, along with failure, make up the twin agents of evil working against anyone who ever attempted something great. The first step in going out on your own has to do with getting over fear, and while everyone says you have to do it, very rarely do they tell you how.
That’s because they can’t. You need tools. You need to develop those tools, and the only way to do it is to face your fear and try to make it less.
It would have been easy for me to lead a lifestyle that just didn’t include flying. Tony Kornheiser from ESPN is famous for this, and he managed to spend an entire season doing color for Monday Night Football going from city to city on a bus.
Yeah. I could have gone that route, but it would have meant a huge hit to my career, my vacation choices, dude weekends in Vegas, and it would have seeped into other areas of my life.
It would be just as easy to give up public speaking because they’re all gonna laugh at me, or public writing because someone might flame me on the Twitter. Today’s world doesn’t even allow you to consider the risk when opportunity knocks, let alone debate it. When good things happen, they happen fast.
It took me 15 years, 100 miserable flights, weeks and months of dark clouds circling my head in preparation for those flights, and an answer that doesn’t leave me fear-free, but gives me the tools I need to handle it. That’s the key. Now I can say yes, in a heartbeat, to just about anything, and I’ll let the chips fall where they may.
I’m still going to be afraid, but now I know how to deal with it. And if I can get over something as long-term and difficult as that, I can get over anything.
I’ve got the tools.
You know that job interview question where the interviewer asks you what your biggest weakness is? It's a punch line at this point -- I've even asked it recently just to see the reaction I'd get from the candidate. I don't recommend this however, as it's neither as insightful nor as funny as it looks on paper.
In the past, I’d always had an answer for this question, and it wasn’t the standard:
• I work too hard.
• I’m a perfectionist.
• I care too much.
My answer was honest and ugly.
“I’m contrarian to a fault. That’s not to say I disagree with everything anyone says. In fact, the opposite, I’m a swell team player. But if you push me in a direction I don’t believe I should go, I will vehemently push back. Hard. Just because. Even if I know I’m going to lose.”
This answer was solid for three reasons:
1) I got to use the word “vehemently” correctly in a sentence.
2) There was rarely any follow up, because the interviewer was really just expecting me to choose one of the above BS answers so they could jump on it.
3) If the company I wanted to work for was worth working for, this was the right answer.
Being contrarian isn't for everyone, because the risk/reward ratio for pulling it off properly is on the high side. Not every person in the working world has this tolerance in their makeup, and usually those that have it don't understand the balance. Those are the mavericks, the daredevils, the rebels -- and we're drawn to them in business just like we're drawn to them in the movies.
But guess what? They lose a lot more often than they win. Those stories are usually less popular and rarely make it onto our radar. Unless the story goes something like win-win-win-lose, at which point we can’t wait to tear them down.
To follow that analogy, the contrarian is much better off going win-fold-win-win-fold and et cetera. You have to know at which point it doesn’t make sense to tilt at the windmill anymore. And that’s the hardest part of it.
What’s worse is when you win when you should have folded, when the stars align and you pull off that last minute victory when you had no business still being in the game, but you were still there butting heads because your ego wouldn’t let you walk.
That’s happened to me a couple times, and I can’t tell you how many follow-ups I had to lose before I got my head back on straight and realized where the fault tolerance was in my modus operandi.
I haven’t interviewed for a job in, I don’t know, 15 years or something like that. But if I were to walk into an interview tomorrow, I wouldn’t talk about my contrarianism as a weakness any more. I’ve learned where the limits are. I still get into trouble, but not the kind that ends up in the unemployment line or court.
So next time I’ll just go with the fact that I tend to shoehorn terms like “modus operandi” into my lexicon to make myself sound smarter than I am when I know full well that it just makes me sound like a jerk.
Entrepreneurs hate rules. Good entrepreneurs break them. Great entrepreneurs rewrite them.
I learned pretty early on to live by that code. And I should preface quickly here with the cautionary advice that this approach to life hasn’t always worked out in my favor. Besides my aforementioned contrarian bent, I also have a stubborn side that has probably kept me from hooking a few brass rings.
Not all rules suck. Most rules are good. There’s this whole societal tipping point being kept in check by most of us adhering to a common agreement of not killing each other to get ahead. But some rules are just stupid, and therein lies a lot of opportunity.
And a lot of heartbreak.
From time to time I'll get tripped up on other people's rules -- these are the ones that make no sense and defy logic. I'll assume that people would expect me to do what I would expect others to do in a given situation, especially when it's something that benefits everyone involved. When that doesn't happen, and the rules force me to do something that benefits no one, I get irked.
We all do. Usually we recoil at rules that have unintended consequences and we're incensed that nobody is keeping an eye on this unchecked glitch in the system. It's usually futile frustration, because most of the time those eyes are blind for a reason -- because that rule that doesn't seem to make sense for anybody actually makes sense for a small group of people, or maybe one person, who has turned that unintended consequence into an undiscovered benefit.
This is why we vote less and complain more.
Government and corporate scenarios present the two best examples of other people’s rules having huge impacts on each of those sectors’ ability to execute. We’ve all heard about those situations in government where you’ve got one set of directives that completely cancel out a second set of directives, which in turn cancel out the first.
Pretzel Logic disguised as For the People.
This usually leads to fraud, or at least I can loosely draw that conclusion based on my own observations. The more you regulate, the more you open the door of opportunity for influence peddling and loophole management.
In Corporate America, the rules tend to weigh down innovation, eventually rusting user experience and then customer care until the whole thing burns and sinks. You see this a lot in the monopolized, commoditized industries -- Energy, Cable, Telecom, Automotive, Retail.
These are places where the establishment has hardened its foundation so deeply that it’s nearly impossible to break in, and when innovation does happen, it’s pent up and explosive. Netflix, iPhone, Tesla, Amazon.
Note that we haven’t cracked energy yet. But there was that $500 million Solyndra government corporate investment project a few years back. I’ll just leave that there.
Oh, and Elon Musk. God bless his crazy brain.
Taking it down to much more personal terms: For an entrepreneur, rule-breaking should be a hobby. There’s money to be made in making sense where sense has lapsed. Another term for that is disruption, but it’s really just the redefining of other people’s rules.
And great entrepreneurs actually like rules. Good rules. Rules that are grounded in logic.
This is what the great entrepreneurs do. When they run up against other people’s rules, the ones that defy logic, they don’t break them, they do everything in their power to rewrite them until they make sense again.
I was at the outdoor patio of a local bar in the middle of our area’s startup hub, enjoying a few beers with an entrepreneur I’m advising. This bar is kind of ground zero for startup talk.
We were preparing for his second fundraising cycle, so we were slinging around startupy terms, but after a couple beers and playing off the excitement we were both feeling around what he was building, the conversation became less numeric and more fun.
That’s when the dude two stools over spoke up.
“Hey, I don’t mean to be eavesdropping on your conversation, but I just want to say the way you guys are talking is pretty cool. I wish I was a part of something like that.”
Or it was something close to that (beers). My first reaction was kind of a warm glow -- that guy just made my day. Then my annoying side kicked in and I responded.
“So… Why aren’t you a part of something like that?”
This turned into a longer conversation over another round. I’m going to call this guy Ernie, because that’s nothing like his name.
Ernie is a family man and holds down a very respectable, important job in the public sector, one that takes a long time to achieve in both education and time served, and it’s a job that if you told your mother you just landed, she’d pick up the phone and start calling her friends.
He’s also very active in his industry and his community. He teaches his craft, and he’s on boards of nonprofits.
Ernie is happy, but he isn’t happy. He’s got ideas. And he has no idea where to go with them.
His ideas, from the two-minute pitch I got, are OK. I can’t speak to whether or not he’s going to change the world, but I do know that his ideas aren’t far enough along to where I can make an assessment and tell him what to do next.
Ernie is at that wait-a-minute point. That moment where he’s amassed strong credentials and a solid career and he’s probably the envy of a bunch of his friends and colleagues, but he’s got that itch, that little voice inside his head casting doubt.
He got into his career to help people, and he’s doing that. But he feels like he can do more, and it’s likely the very structure that he’s fought so hard to get into and advance through that’s holding him back.
Startup, or in fact anything other than the bureaucracy in which he finds himself at this point in his career, would be “liberating.”
But it’s also something else.
“Terrifying,” he said.
The reason why it seems that most entrepreneurs come right out of college or even drop out of college and get into startup at a young age isn’t because they’re naturally more equipped or are better at entrepreneurism than their more seasoned and experienced peers (elders).
It’s because they have nothing to lose. If you’re going to dine on Ramen every day and stare down the barrel of student debt, you might as well take a chance on your own thing.
But there’s another reason startup seems like a kid’s game, and that’s because those kids haven’t been programmed yet.
Much like a musician or a writer or an artist, as an entrepreneur you've got to be ALL IN on what you're doing, and you've got to come to grips with the fact that those established tokens of success -- the right house, the expensive car, the eff-you money -- might not happen for you. There's also no roadmap, no career ladder, and -- even despite all the interest around startup these days -- still very little in terms of support or education.
However, unlike rock stars and running backs, the life expectancy of an entrepreneur doesn't end at 30. There's no ticking clock other than the one in your head. But those ticks get amplified when you see people achieve all those success tokens -- the corner office, the sales trips to Vegas, the tailored suits -- whatever it may be.
Ernie put it like this: “I’m probably, at this point, a company man.”
No, Ernie. No you’re not.
There’s no one single path to independence, just like there’s no one single path to being successful once you get there.
Startup doesn’t require that you ditch and unlearn everything you’ve fought so hard for. You don’t need to quit your job this minute in some Zen-like moment of self-discovery. That would indeed be terrifying. You don’t have to blow the kids’ education fund on offshore development of your app. You don’t even have to spend the couple hundred dollars to incorporate.
Startup is not about risking everything on one roll of the dice. It isn’t about your job at all. It’s about that wait-a-minute feeling that my buddy Ernie is having right now, and doing something, anything, every single day to bring that idea a little closer to reality. It’s about confronting that voice of doubt and living your life doing what you truly want to do, not trying to be what you think you should be.
Frustration and fear kill way more entrepreneurial careers than running out of money does.
In that sense, when done right, startup can actually be kinda boring. Maybe even maddening. But it’s also something you can be a part of.
I had a conversation with a guy who was itching to get into something entrepreneurial, but didn’t consider himself to be an entrepreneur.
He had so far spent his career doing something in finance. In fact, he looked like he had just come from the office. So I told him what I tell people who come to me looking like they’re coming to me directly from their job.
Just because you’re not holding the magic line of code that’s going to create the next insert-hot-unicorn here, doesn’t mean you shouldn’t get involved with startup.
Despite what you might hear about a dearth of technical talent in this country, startup already has its share of technicians, visionaries, game-changers and rock stars. What we don’t have are enough people who can design, manage, market, sell, and grow a startup product to the next level.
When you launch a product, it’s hard to sell your first few units, but then surprisingly easy to sell your next bunch. After that, it gets to be nearly impossible to sell much more. Building sustainable sales channels, establishing recurring revenue, expanding market share and crushing churn—these are things entrepreneurs aren’t very good at.
So if you’re coming from your day job and looking to make the leap into startup, I said, find somebody with a vision you believe in. Then find a dozen more, get to know them, and when the time is right, get involved. You probably won’t find what you want right away, but at least you’ll have a pipeline.
Then I asked what got him interested in startup. You know, to make small talk.
“Well,” he said, “It’s not a startup or anything, but I make these.”
He reached into his pocket and pulled out a beautifully crafted leather wallet. He hand stitches them. He learned how to do everything by doing research on the Internet.
He discussed the differences between hand-stitching and machine-stitching, the different kinds of leather, and the dreaded “Costanza effect.” He explained all this in a way that I could easily understand.
That’s when I told him he was perfect for startup.
That kind of passion is necessary if you want to found, join, or build a startup. No wait, let me rephrase that. That kind of passion, combined with the determination and work ethic to learn and do what it takes to go from initial idea to a final product you can carry around in your pocket—that’s what’s necessary if you want to found, join, or build a startup.
It’s not everything you need, but it sure means more than being able to sling lines of code or create the perfect pitch deck.
By the time he was done explaining how his wallet was made, he had so outlined the superiority of his product that I wanted to buy one, right there on the spot.
Show me the startup founder who doesn’t want someone like that on board and I’ll show you a poser.
I think sometimes in startup we tend to overlook the talent that’s out there in Corporate America and even the public and nonprofit sectors. We’re not afraid to poach technical talent from these areas, but for one reason or another we eschew marketers, managers, salespeople, finance people, basically everything except coding.
We fear that they like the nine-to-five, they won’t be able to keep pace, they don’t know how to sell or market or manage a new product. We think they’ll cost too much. We get concerned that they’ve gotten too comfortable.
I don’t know that that’s true. I meet more and more people who are stuck pushing powerpoints and spreadsheets at corporate jobs who would kill to join a company that cares about the product it’s producing, especially if it’s a product those people care about themselves.
We’re going to need more people like this. The great news is, they’re already here. They’re wearing suits to work every day. Maybe they’re not playing ping pong or having beer Fridays. Maybe they’ve never seen your widget before, but maybe they just closed a seven-figure book of business for someone else’s widget.
Yeah, Corporate America used to be comfortable, but it isn’t anymore. Corporate America is waking up to mass layoffs, fewer perks, meetings to talk about meetings, and the slippery, shaky corporate ladder. They’re VPs in a sea of VPs, and they’re starting to see the light.
Or maybe I’m talking to you. Maybe you’re slogging through Corporate America because you think it’s the safer and wiser choice.
If the security of a steady job is keeping you from taking control of your own destiny, you’re buying someone else’s story.
Job security is a myth designed to keep people unhappy and underpaid. If you want to get paid what you’re really worth, you’re not going to find that in Corporate America.
Of course, the flip side is that there are a ton of people in Corporate America being paid way more than they’re worth. You can probably think of a dozen or so right now, off the top of your head.
There’s another great reason to make the leap.
The other day, my daughter asked me when I was going to retire. It was the first time that the word had made it into her vocabulary and it was the first time I’d ever been asked that question outside of some cold-calling banker looking to get his hands on what he assumed to be my massive 401k balance (joke’s on you, buddy!).
I thought about her innocent little question for a moment and then told her the first answer that came to my mind. “You know what,” I said, “I’m probably not going to retire.”
Now, if that scene were a television commercial for a brokerage or a politician, the camera would freeze-frame on me with what-am-I-gonna-do face, and then either financial advice or rhetoric about the incumbent would be thrown at you.
It’s not going to be a financial decision, although I’ll be the first to tell you that the financial promise of retirement for me has always been and continues to be about 50/50.
But what the hell would I do?
And why would I suddenly decide to hang it up?
Don't get me wrong. I understand why people retire and I definitely understand why people look forward to retirement. My best friend is planning to retire when he hits 55, and he'll be able to do it and he won't look back for a second. As much as he and I are alike -- same background, same upbringing, roughly the same personality and even the same height -- we're polar opposites in the career department.
He’s a double super senior executive vice president at a large corporation that handles a lot of financial transactions for individuals and businesses. He’s got a great office, mostly plays golf and drinks with clients, a company car, seven-and-a-half weeks of vacation, and an attractive retirement plan that he’s been cramming every disposable penny into since the day he left college.
My life is… different, in some ways better and in some ways not as good. Sometimes he calls me at 9:00 p.m. when I’m in the middle of some last-minute rush to production and he’s coming off the golf course and Uber-ing his way home. He loves when this happens, because he gets to rub it in.
Then other times he asks me things like am I sure my boss will give me a week off of work in the middle of January to go to Vegas and I’m all like “I don’t know, I’m kind of a hardass about that.”
Actually, don’t tell him this, but I am kind of a hardass about that, and I never disconnect from work completely. But that’s another reason why I probably won’t retire.
Kids, save for retirement.
I too have shoveled money into various 401ks and IRAs and Roths along this crazy startup path. One of the first things I did when I started my first company was set up a retirement plan attached to that company. I highly recommend that.
My point is that work isn’t something I punch into and out of at 9:00 and 5:00 from Monday to Friday. And on the flip side, I can’t remember ever looking up at the clock at 2:00 pm on a Tuesday and thinking “Oh man, it’s only 2:00 pm. When will this Tuesday end?”
So honestly, am I racing to get to the point where I can quit working completely so I can go play golf in the middle of the day?
Well, hell, I can go play golf in the middle of the day already. I don’t. But I could.
And that’s the kicker. The entire concept of retirement is foreign to me and, to be naively truthful with you, I pretty much live what I consider to be a semi-retired life now. I get up in the morning, and I do what I do. I wouldn’t do it for free, but for the most part, it’s kinda fun.
I don’t know, I guess I could play Xbox all day. That’d be fun for a week.
One of my greatest fears is waking up 15 years later and realizing my goals had been wrong the whole time. It’s the reason I constantly reassess where my happiness comes from and reset my path every once in awhile.
That fear includes waking up one day and my kids are all grown up and I'm sitting on a pile of money that -- well, shoot -- what am I going to do with it when I'm 70? I go to casinos a lot. Those are the places where I see the most old people gathered in one room. It doesn't look like fun. In fact, I've told all my gambling buddies that if we're not getting comped in suites and playing in the high-roller rooms by the time we reach our 50s, I'm out.
My best friend has the right path for him. He wants to put in his 30 years and be done. His energy, and his money, goes into that.
On the other hand, I spent a ton of money in my 20s – well, a ton as a percentage of my income -- doing things like traveling, partying, and taking on everything from new hobbies to new businesses just because I wanted to try stuff. I don't regret any of that for a second. I paid my bills and dues along the way.
And guess what? Still paying them.
Now I’m spending tons on my kids and their education and well-roundedness. Not so much the partying and the traveling, but maybe the occasional trip to Disneyworld.
So when people say they’re going to step aside from their job to spend more time with their family, well, we all know that’s usually a smokescreen, but I’m always like, why didn’t they just integrate their family into their lives a little more before? When it mattered.
I expect to still be paying dues and bills in the future. That doesn’t stop, right? Social Security, Medicare, Medicare supplement plans, the freaking AARP? Sounds like there’s a whole industry just to deal with my upcoming medical bills.
So yeah, I’m stowing away a healthy chunk of change to make sure I don’t die of the vapors. And if something goes horribly wrong, I don’t want to be a burden to my kids. But I think of that money as emergency money. Maybe someday I won’t be able to work anymore, but I just don’t see a future in which I’m not thinking about what’s next.
You’re dead at that point anyway, right?
Who knows? Maybe I’ll see the light someday and buy an RV and see the country. Again. I’m just pretty sure I’ll have some sneaky business plan tucked into the sun visor, stopping to see potential customers along the way.
OK, you’ve reached the end. And again, thank you, I really hope you enjoyed this and you found some value in it.
Remember, THIS IS JUST A PREVIEW of Entrepreneur Life. If you liked this, go pick that up. It’s tons more and it’s the better stuff.
And speaking of tons more, you can get that at:
I’d also encourage you to get the books on the two pages that follow the Entrepreneur Life cover. You can find all the books wherever books are sold.
THIS IS A PREVIEW of another book called Entrepreneur Life. My hope is that you'll read this first, get something out of it, and then put up the money for the whole book. You can get that book where you got this one, or anywhere you can buy books. Entrepreneur Life is a startup book for everyone, from people just starting out to people who have done startup more than once. This is not what you'd expect out of a startup book. It goes against the grain of everything that's being sold as startup culture today. It's not hip, it's not trendy, and it's not a bunch of commandments, rules and slogans coming down from on high. This is about a new way to look at entrepreneurism, and it's about independence, freedom, growth, achievement, happiness, and success, no matter what it is that you start. The earlier chapters link to the earlier part of startup. And that's what you're getting here in The Jump. As you get deeper into running your own company, the later chapters of Entrepreneur Life will apply a little more directly. But I hope it's all valuable and applicable, no matter where you are on your journey. Look, there are a lot of people out there like you. Startup is not an exclusive club. It's not a rite of passage. It's not about board seats and billions of dollars. It's about waking up every day and doing what you love. That’s what this book is about. Currently, I'm at Automated Insights, a company that makes software that automatically writes narrative content from raw data. I've been at Ai since 2010, and while I was there I founded ExitEvent in my spare time. ExitEvent is a startup network and news source, and in three years it became the most widely-read startup media site in the Southeast. I sold ExitEvent in 2013. Ai was acquired in 2015. Since then, I've been investing in startups, meeting with founders, mentoring, advising, all of that cool stuff you get to do when you exit. But none of that made sense to me. I was able to help a handful of people at a time, and I found I was saying a lot of the same stuff over and over. I needed to scale. This book is a part of that effort. So look at this book as a series of coffee or beer meetings (or whatever you want to drink, I'm not going to judge you) with someone who has been there, and has spent years talking to other people who are in your shoes. Even if you pay ten times as much for this book, you'll be saving on buying drinks. That alone makes it worth it, right?